Hydrochloric Acid → 4-Hydroxy-4-(trifluoromethyl)cyclohexan-1-one

HRID 509285Notes

Reaction equation

HRID 509285 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1([OH:13])[CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5][CH2:4]1.Cl>C1COCC1>[OH:13][C:3]1([C:2]([F:1])([F:14])[F:15])[CH2:4][CH2:5][C:6](=[O:7])[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 616452568-(Trifluoromethyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 200351424-Hydroxy-4-(trifluoromethyl)cyclohexan-1-oneYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-(trifluoromethyl)-1,4-dioxaspiro[4.5]decane-8-ol (2.0 g, 8.84 mmol) was dissolved in THF (30 ml), followed by addition of 1N aqueous HCl solution (15 ml), and then the resulting mixture was stirred at room temperature for 24 hours. The resulting reaction liquid was concentrated under reduced pressure, and then extracted with 10% MeOH/MC (15 ml×6). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (40% EtOAc/Hexanes), to obtain 1.24 g of white solid (77%).

Workup

  1. customThe resulting reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. extractionextracted with 10% MeOH/MC (15 ml×6)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfollowed by filtration and concentration
  6. customthe residue thus obtained

Sources & evidence

ORD record
ord-a72d30933d7d49a3936afa3b44dfca4c
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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